3-methylbenzoselenazolinone | 142776-62-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3-methylbenzoselenazolinone
• 英文别名: 3-methyl-3H-benzoselenazol-2-one；3-Methyl-3H-benzoselenazol-2-on；3-Methyl-1,3-benzoselenazol-2-one
• CAS: 142776-62-3
• 化学式: C₈H₇NOSe
• 分子量: 212.11
• InChiKey: MBMMDQLESIQUHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methylbenzoselenazolinone 在 tetraphosphorus decasulfide 作用下， 生成 N-methyl-3H-benzoselenazole-2-thione
  参考文献：
  名称：

  414.杂环化合物的不饱和度和互变异构性。第七部分 硒唑衍生物

  摘要：

  DOI：

  10.1039/jr9350001762
• 作为产物：
  描述：

  双(2-氨苯基)二硒 在 吡啶 、 盐酸 、 tin 、 sodium ethanolate 作用下， 反应 0.25h， 生成 3-methylbenzoselenazolinone
  参考文献：
  名称：

  Benzoselenazolinone Derivatives Designed To Be Glutathione Peroxidase Mimetics Feature Inhibition of Cyclooxygenase/5-Lipoxygenase Pathways and Anti-inflammatory Activity

  摘要：

  Two series of compounds, substituted benzoselenazolinones and their opened analogs, diselenides, mere prepared. The diselenides were designed according to the available SAR about glutathione peroxidase mimics and were expected to have activity. An initial series of tests was performed in order to assess the glutathione peroxidase and antioxidant activity of the diselenides compared to their cyclized analogs. The diselenides were shown to be very potent (up to 3 times the activity of ebselen), whereas the benzoselenazolinones were inactive, thus confirming our hypothesis. A second series of tests was done to determine the anti-inflammatory potency of the two series. Both were found to be potent on cyclooxygenase and 5-lipoxygenase pathways (up to 95% inhibition at 10(-5) M). Some compounds were selective, and the variations in the activity allowed us to draft some structure-activity relationships. The most interesting compound of each series, 6-benzoylbenzoselenazolinone and bis[(2-amino-5-benzoyl)phenyl] diselenide, was tested in vivo on the rat foot edema induced with different phlogistic agents and was shown to have some anti-inflammatory properties.

  DOI：

  10.1021/jm00044a011

文献信息

• Regioselective Acylation of Benzoselenazolinone
  作者：V. Galet、M. P. Vaccher、J. L. Bernier、J. P. Henichart、D. Lesieur

  DOI：10.1080/00397919308009820

  日期：1993.3.1

  benzoselenazolinone were performed by using successively (i) aliphatic or aromatic acids and (ii) acid chlorides in the presence of (i) polyphosphoric acid and (ii) aluminium chloride in dimethylformamide. Regioselective acylation at C6 position was demonstrated by 1H NMR using Nuclear Overhauser Effect.

  摘要 在二甲基甲酰胺中，在 (i) 多磷酸和 (ii) 氯化铝存在下，依次使用 (i) 脂肪族或芳香族酸和 (ii) 酰氯对苯并硒唑啉酮进行取代。C6 位置的区域选择性酰化通过 1H NMR 使用核 Overhauser 效应证明。
• Experimental and Theoretical Studies on the Thermal Decomposition of Heterocyclic Nitrosimines¹
  作者：Richard A. Bartsch、Yeh Moon Chae、Sihyun Ham、David M. Birney

  DOI：10.1021/ja010659k

  日期：2001.8.1

  A series of substituted 2-nitrosiminobenzothiazolines (2) were synthesized by the nitrosation of the corresponding 2-iminobenzothiazolines (6). Thermal decomposition of 2a-f and of the seleno analogue 7 in methanol and of 3-methyl-2-nitrosobenzothiazoline (2a) in acetonitrile, 1,4-dioxane, and cyclohexane followed first-order kinetics. The activation parameters for thermal deazetization of 2a were measured in cyclohexane (DeltaH(double dagger) = 25.3 +/- 0.5 kcal/mol, DeltaS(double dagger) = 1.3 +/- 1.5 eu) and in methanol (DeltaH(double dagger) = 22.5 +/- 0.7 kcal/mol, DeltaS(double dagger) = -12.9 +/- 2.1 eu). These results indicate a unimolecular decomposition and are consistent with a proposed stepwise mechanism involving cyclization of the nitrosimine, followed by loss of N-2. The ground-state conformations of the parent nitrosiminothiazoline (9a) and transition states for rotation around the exocyclic C=N bond, electrocyclic ring closure, and loss of N-2 were calculated using A initio molecular orbital theory at the MP2/6-31G* level. The calculated gas-phase barrier height for the loss of N-2 from 9a (25.2 kcal/mol, MP4(SDQ, FC)/6-31G*//MP2/6-31G* + ZPE) compares favorably with the experimental barrier for 2a of 25.3 kcal/mol in cyclohexane. The potential energy surface is unusual; the rotational transition state 9a-rot-ts connects directly to the orthogonal transition state for ring-closure 9aTS. The decoupling of rotational and pseudopericyclic bond-forming transition states is contrasted with the single pericyclic transition state (15TS) for the electrocyclic ring-opening of oxetene (15) to acrolein (16). For comparison, the calculated homolytic strength of the N-NO bond is 40.0 kcal/mol (MP4(SDQ, FC)/6-31G*//MP2/6-31G* + ZPE).
• Benzoselenazolinone Derivatives Designed To Be Glutathione Peroxidase Mimetics Feature Inhibition of Cyclooxygenase/5-Lipoxygenase Pathways and Anti-inflammatory Activity
  作者：Vincent Galet、Jean-Luc Bernier、Jean-Piere Henichart、Daniel Lesieur、Claire Abadie、Luc Rochette、Albert Lindenbaum、Jacqueline Chalas、Jean-Francois Renaud de la Faverie

  DOI：10.1021/jm00044a011

  日期：1994.9

  Two series of compounds, substituted benzoselenazolinones and their opened analogs, diselenides, mere prepared. The diselenides were designed according to the available SAR about glutathione peroxidase mimics and were expected to have activity. An initial series of tests was performed in order to assess the glutathione peroxidase and antioxidant activity of the diselenides compared to their cyclized analogs. The diselenides were shown to be very potent (up to 3 times the activity of ebselen), whereas the benzoselenazolinones were inactive, thus confirming our hypothesis. A second series of tests was done to determine the anti-inflammatory potency of the two series. Both were found to be potent on cyclooxygenase and 5-lipoxygenase pathways (up to 95% inhibition at 10(-5) M). Some compounds were selective, and the variations in the activity allowed us to draft some structure-activity relationships. The most interesting compound of each series, 6-benzoylbenzoselenazolinone and bis[(2-amino-5-benzoyl)phenyl] diselenide, was tested in vivo on the rat foot edema induced with different phlogistic agents and was shown to have some anti-inflammatory properties.
• 414. The unsaturation and tautomeric mobility of heterocyclic compounds. Part VII. Selenazole derivatives
  作者：Chiragh Hasan、Robert F. Hunter

  DOI：10.1039/jr9350001762

  日期：——